Literature DB >> 22140280

Total syntheses of isonaamine C and isonaamidine E.

Heather M Lima1, Beatriz J Garcia-Barboza, Nicole N Khatibi, Carl J Lovely.   

Abstract

The total syntheses of two alkaloids isolated from a marine sponge of the Leucetta sp. have been accomplished in 6 and 7 steps starting from a 4,5-diiodoimidazole derivative. Grignard mediated halogen-metal exchange was used to install the benzyl side chain. C2 substitution was accomplished via lithiation followed by quenching with trisyl azide which provided isonaamine C after hydrogenation. Isonaamidine E was then prepared from isonaamine C via introduction of the hydantoin ring by reaction with an activated parabanic acid.

Entities:  

Year:  2011        PMID： 22140280      PMCID： PMC3225899          DOI： 10.1016/j.tetlet.2011.08.030

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  8 in total

Review 1.  Structure and synthesis of 2-aminoimidazole alkaloids from Leucetta and Clathrina sponges.

Authors:  Panduka B Koswatta; Carl J Lovely
Journal:  Nat Prod Rep       Date:  2010-10-28       Impact factor: 13.423

2.  A concise total synthesis of naamidine A.

Authors:  Nicholas S Aberle; Guillaume Lessene; Keith G Watson
Journal:  Org Lett       Date:  2006-02-02       Impact factor: 6.005

3.  The Mg-oppenauer oxidation as a mild method for the synthesis of aryl and metallocenyl ketones.

Authors:  Ralf J Kloetzing; Arkady Krasovskiy; Paul Knochel
Journal:  Chemistry       Date:  2007       Impact factor: 5.236

4.  Total Syntheses of Naamidine G and 14-Methoxynaamidine G.

Authors:  Panduka B Koswatta; Carl J Lovely
Journal:  Tetrahedron Lett       Date:  2010-01-06       Impact factor: 2.415

5.  Total synthesis of (+/-)-calcaridine A and (+/-)-epi-calcaridine A.

Authors:  Panduka B Koswatta; Rasapalli Sivappa; H V Rasika Dias; Carl J Lovely
Journal:  Org Lett       Date:  2008-09-25       Impact factor: 6.005

6.  Highly functionalized organomagnesium reagents prepared through halogen-metal exchange.

Authors:  Paul Knochel; Wolfgang Dohle; Nina Gommermann; Florian F Kneisel; Felix Kopp; Tobias Korn; Ioannis Sapountzis; Viet Anh Vu
Journal:  Angew Chem Int Ed Engl       Date:  2003-09-22       Impact factor: 15.336

7.  Uniquely modified imidazole alkaloids from a calcareous Leucetta sponge.

Authors:  Ru Angelie Edrada; Chad C Stessman; Phillip Crews
Journal:  J Nat Prod       Date:  2003-07       Impact factor: 4.050

8.  New and biologically active imidazole alkaloids from two sponges of the genus Leucetta.

Authors:  Harald Gross; Stefan Kehraus; Gabriele M König; Gert Woerheide; Anthony D Wright
Journal:  J Nat Prod       Date:  2002-08       Impact factor: 4.050
  8 in total
  3 in total

1.  Total synthesis of 7'-desmethylkealiiquinone.

Authors:  Heather M Lima; Rasapalli Sivappa; Muhammed Yousufuddin; Carl J Lovely
Journal:  Org Lett       Date:  2012-04-24       Impact factor: 6.005

2.  Total synthesis and cytotoxicity of Leucetta alkaloids.

Authors:  Panduka B Koswatta; Sabha Kasiri; Jayanta K Das; Arunoday Bhan; Heather M Lima; Beatriz Garcia-Barboza; Nicole N Khatibi; Muhammed Yousufuddin; Subhrangsu S Mandal; Carl J Lovely
Journal:  Bioorg Med Chem       Date:  2017-01-20       Impact factor: 3.641

3.  Studies Towards the Leucetta-derived Alkaloids Spirocalcaridine A and B - Possible Biosynthetic Implications.

Authors:  Panduka B Koswatta; Jayanta Das; Muhammed Yousufuddin; Carl J Lovely
Journal:  European J Org Chem       Date:  2015-04
  3 in total

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